CS236457B2 - Method of pure methyl-tert.buthylether and hydrocarbon mixture simultaneous production with 4 isobutene-free carbon atoms - Google Patents
Method of pure methyl-tert.buthylether and hydrocarbon mixture simultaneous production with 4 isobutene-free carbon atoms Download PDFInfo
- Publication number
- CS236457B2 CS236457B2 CS798765A CS876579A CS236457B2 CS 236457 B2 CS236457 B2 CS 236457B2 CS 798765 A CS798765 A CS 798765A CS 876579 A CS876579 A CS 876579A CS 236457 B2 CS236457 B2 CS 236457B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- column
- hour
- isobutene
- tert
- reaction
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 title claims description 35
- 229930195733 hydrocarbon Natural products 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 175
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 71
- 238000006243 chemical reaction Methods 0.000 claims description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 235000019441 ethanol Nutrition 0.000 claims description 18
- -1 olefin tetrate Chemical class 0.000 claims description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 54
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 49
- 239000000047 product Substances 0.000 description 48
- 150000001336 alkenes Chemical class 0.000 description 24
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 21
- 239000001273 butane Substances 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 2
- KLIHWYNSISMOMR-UHFFFAOYSA-N 2,2,3-trimethylpentan-3-ol Chemical compound CCC(C)(O)C(C)(C)C KLIHWYNSISMOMR-UHFFFAOYSA-N 0.000 description 1
- FTGPSKPJRKRPSX-UHFFFAOYSA-N 2-butoxy-2-methylbutane Chemical compound CCCCOC(C)(C)CC FTGPSKPJRKRPSX-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000035617 depilation Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical class CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/14875—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds
- C07C7/14891—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound with organic compounds alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Water Supply & Treatment (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2853769A DE2853769C3 (de) | 1978-12-13 | 1978-12-13 | Verfahren zur gleichzeitigen Herstellung von reinem Methyl-tert.-butylether und einem C↓4↓-Kohlenwasserstoffgemisch, das wesentlich weniger als 1% Isobuten enthält |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS236457B2 true CS236457B2 (en) | 1985-05-15 |
Family
ID=6057031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS798765A CS236457B2 (en) | 1978-12-13 | 1979-12-13 | Method of pure methyl-tert.buthylether and hydrocarbon mixture simultaneous production with 4 isobutene-free carbon atoms |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4282389A (en, 2012) |
| JP (1) | JPS5592326A (en, 2012) |
| AR (1) | AR218791A1 (en, 2012) |
| AT (1) | AT370713B (en, 2012) |
| BE (1) | BE880581A (en, 2012) |
| BR (1) | BR7908129A (en, 2012) |
| CA (1) | CA1128552A (en, 2012) |
| CS (1) | CS236457B2 (en, 2012) |
| DD (1) | DD147664A5 (en, 2012) |
| DE (1) | DE2853769C3 (en, 2012) |
| ES (1) | ES486823A1 (en, 2012) |
| FI (1) | FI69052C (en, 2012) |
| FR (1) | FR2444021A1 (en, 2012) |
| GB (1) | GB2040924B (en, 2012) |
| HU (1) | HU182501B (en, 2012) |
| IL (1) | IL58936A (en, 2012) |
| IT (1) | IT1164090B (en, 2012) |
| NL (1) | NL7908945A (en, 2012) |
| NO (1) | NO149659C (en, 2012) |
| PL (1) | PL220320A1 (en, 2012) |
| PT (1) | PT70318A (en, 2012) |
| RO (1) | RO79319A (en, 2012) |
| SE (1) | SE445110B (en, 2012) |
| SU (1) | SU1367854A3 (en, 2012) |
| YU (1) | YU39574B (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2629769C3 (de) * | 1976-07-02 | 1989-03-16 | Hüls AG, 4370 Marl | Verfahren zur Herstellung von reinem Methyl-tertiär-butyläther |
| DE3024147C2 (de) * | 1980-06-27 | 1983-05-05 | Edeleanu Gmbh, 6000 Frankfurt | Verfahren zur Auftrennung der bei der Verätherung von niederen i-Olefinen mit Methanol anfallenden Reaktionsprodukte |
| DE3036481A1 (de) * | 1980-09-27 | 1982-05-19 | EC Erdölchemie GmbH, 5000 Köln | Verfahren zur gemeinsamen herstellung von c 4 -oligomeren und alkyl-tert.-butylethern |
| DE3116779A1 (de) * | 1981-04-28 | 1982-11-04 | Veba Oel AG, 4660 Gelsenkirchen-Buer | Verfahren zur herstellung von alkoholen und aethern |
| DE3116780A1 (de) * | 1981-04-28 | 1982-11-04 | Veba Oel AG, 4660 Gelsenkirchen-Buer | Verfahren zur herstellung von sec.-butylalkohol und sec.-butyl-tert.-butylether |
| US4371718A (en) * | 1981-07-02 | 1983-02-01 | Phillips Petroleum Company | Using butenes to fractionate methanol from methyl-tertiary-butyl ether |
| DE3148109A1 (de) * | 1981-12-04 | 1983-06-09 | EC Erdölchemie GmbH, 5000 Köln | Verfahren zur herstellung von methyl-tert.-butylether (mtbe) und weitgehend von i-buten und vom methanol befreiten kohlenwasserstoff-raffinaten |
| US4413150A (en) * | 1981-12-18 | 1983-11-01 | Uop Inc. | Two product process for methyl tertiary butyl ether production |
| US4510022A (en) * | 1983-08-08 | 1985-04-09 | Lloyd Berg | Separation of isopropyl ether from isopropanol and water by extractive distillation |
| US4558168A (en) * | 1985-06-19 | 1985-12-10 | Air Products And Chemicals, Inc. | Production of high purity butene-1 from an n-butane feedstock |
| US4571439A (en) * | 1985-07-22 | 1986-02-18 | Tenneco Oil Company | Method for controlled oligomerization/etherification of propylene |
| US4797133A (en) * | 1986-12-29 | 1989-01-10 | Uop Inc. | Process for recovery of butene-1 from mixed C4 hydrocarbons |
| US4761504A (en) * | 1986-12-29 | 1988-08-02 | Uop Inc. | Integrated process for high octane alkylation and etherification |
| US4925989A (en) * | 1987-06-01 | 1990-05-15 | Texaco Inc. | MTBE preparation from isobutylene/TBA and methanol in presence of an acid resin catalyst |
| US5210327A (en) * | 1992-05-15 | 1993-05-11 | Uop | Etherification with skeletal olefin isomerization |
| US5276212A (en) * | 1992-12-29 | 1994-01-04 | Uop | Etherification with intermediate skeletal olefin isomerization |
| RU2102375C1 (ru) * | 1995-08-07 | 1998-01-20 | Товарищество с ограниченной ответственностью "Научно-исследовательский центр по нефтехимическим технологиям" | Способ получения алкил-трет.алкиловых эфиров и их смесей с углеводородами |
| US5985100A (en) * | 1995-08-30 | 1999-11-16 | Basf Aktiengesellschaft | Process for separating butanol and dibutyl ether by means of dual-pressure distillation |
| RU2131865C1 (ru) * | 1998-02-19 | 1999-06-20 | Общество с ограниченной ответственностью "НИЦ НХТ" | Способ получения алкил-трет-алкиловых эфиров или их смесей |
| RU2131866C1 (ru) * | 1998-03-31 | 1999-06-20 | Товарищество с ограниченной ответственностью "НИЦ НХТ" | Способ получения алкил-трет-алкиловых эфиров или их смесей |
| US6660898B1 (en) * | 2000-11-03 | 2003-12-09 | Fortum Oil & Gas Oy | Process for dimerizing light olefins to produce a fuel component |
| EP1388528B1 (de) | 2002-08-06 | 2015-04-08 | Evonik Degussa GmbH | Verfahren zur Oligomerisierung von Isobuten in n-Buten-haltigen Kohlenwasserstoffströmen |
| RU2228923C1 (ru) * | 2003-03-11 | 2004-05-20 | Павлов Дмитрий Станиславович | Способ переработки изобутенсодержащей углеводородной смеси |
| RU2286984C1 (ru) * | 2005-06-20 | 2006-11-10 | Олег Станиславович Павлов | Способ переработки изобутенсодержащей углеводородной смеси |
| DE102005062699A1 (de) * | 2005-12-28 | 2007-09-06 | Oxeno Olefinchemie Gmbh | Verfahren zur Feinreinigung von 1-Buten-haltigen Strömen |
| JP6350259B2 (ja) * | 2013-12-27 | 2018-07-04 | 東レ株式会社 | 芳香族化合物異性体の製造方法 |
| BR112017006109A2 (pt) | 2014-09-26 | 2017-12-19 | Ifp Energies Now | aluminosilicato cristalino modificado para desidratação de álcoois |
| CN105859530B (zh) * | 2015-01-23 | 2018-04-06 | 上海优华系统集成技术有限公司 | 一种稳定塔与mtbe装置催化精馏塔联合循环设备 |
| WO2017005719A1 (en) | 2015-07-09 | 2017-01-12 | Total Research & Technology Feluy | Modified crystalline aluminosilicate for dehydration of alcohols |
| UA123237C2 (uk) | 2016-09-09 | 2021-03-03 | Тотал Ресьоч Е Текнолоджі Фелюі | Спосіб дегідратації моноспирту(ів) з використанням модифікованого кристалічного алюмосилікату |
| US11505516B2 (en) * | 2017-07-19 | 2022-11-22 | Sabic Global Technologies B.V. | Use of MTBE raffinate in the production of propylene |
| CN113058283A (zh) * | 2021-03-01 | 2021-07-02 | 中国石油化工股份有限公司 | Mtbe装置甲醇回收系统及工艺 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1012686B (it) * | 1974-05-21 | 1977-03-10 | Snam Progetti | Procedimento per la preparazione di eteri ter alchilici |
| IT1012690B (it) * | 1974-05-21 | 1977-03-10 | Snam Progetti | Procedimento per la produzione di eteri ter alchilici |
| US3940450A (en) * | 1974-12-16 | 1976-02-24 | Texaco Inc. | Preparation and recovery of ethers |
| FR2312483A1 (fr) * | 1975-05-30 | 1976-12-24 | Erap | Procede de fabrication d'un alkyl tertiobutyl-ether a partir d'une coupe d'hydrocarbures en c4 |
| DE2629769C3 (de) * | 1976-07-02 | 1989-03-16 | Hüls AG, 4370 Marl | Verfahren zur Herstellung von reinem Methyl-tertiär-butyläther |
| DE2705538A1 (de) * | 1977-02-10 | 1978-08-17 | Basf Ag | Verfahren zur reindarstellung von methyl-tert.-butylaether |
| US4148695A (en) * | 1978-07-27 | 1979-04-10 | Texaco Inc. | Preparation and recovery of ethers |
-
1978
- 1978-12-13 DE DE2853769A patent/DE2853769C3/de not_active Expired
-
1979
- 1979-10-16 PT PT70318A patent/PT70318A/pt unknown
- 1979-11-30 AR AR279111A patent/AR218791A1/es active
- 1979-12-03 NO NO793925A patent/NO149659C/no unknown
- 1979-12-04 US US06/100,058 patent/US4282389A/en not_active Expired - Lifetime
- 1979-12-04 FR FR7929755A patent/FR2444021A1/fr active Granted
- 1979-12-06 YU YU2970/79A patent/YU39574B/xx unknown
- 1979-12-10 FI FI793844A patent/FI69052C/fi not_active IP Right Cessation
- 1979-12-10 SE SE7910153A patent/SE445110B/sv not_active IP Right Cessation
- 1979-12-11 IT IT51047/79A patent/IT1164090B/it active
- 1979-12-11 PL PL22032079A patent/PL220320A1/xx unknown
- 1979-12-11 CA CA341,648A patent/CA1128552A/en not_active Expired
- 1979-12-12 BE BE0/198539A patent/BE880581A/fr not_active IP Right Cessation
- 1979-12-12 BR BR7908129A patent/BR7908129A/pt unknown
- 1979-12-12 IL IL58936A patent/IL58936A/xx not_active IP Right Cessation
- 1979-12-12 NL NL7908945A patent/NL7908945A/nl not_active Application Discontinuation
- 1979-12-12 GB GB7942889A patent/GB2040924B/en not_active Expired
- 1979-12-12 DD DD79217602A patent/DD147664A5/de not_active IP Right Cessation
- 1979-12-12 RO RO7999517A patent/RO79319A/ro unknown
- 1979-12-12 ES ES486823A patent/ES486823A1/es not_active Expired
- 1979-12-12 AT AT0783179A patent/AT370713B/de not_active IP Right Cessation
- 1979-12-12 SU SU792853139A patent/SU1367854A3/ru active
- 1979-12-13 JP JP16089979A patent/JPS5592326A/ja active Granted
- 1979-12-13 HU HU79HU298A patent/HU182501B/hu not_active IP Right Cessation
- 1979-12-13 CS CS798765A patent/CS236457B2/cs unknown
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